Methanol → 6-(Trifluoromethyl)-2,3-dihydro-1H-inden-1-OL

HRID 2387434Notes

Reaction equation

HRID 2387434 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][C:9]2=[O:12])=[CH:5][CH:4]=1.[BH4-].[Na+].CO>C1COCC1>[F:1][C:2]([F:13])([F:14])[C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[OH:12])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 227541286-(Trifluoromethyl)-1-indanone

Product 1

HCID 592126636-(Trifluoromethyl)-2,3-dihydro-1H-inden-1-OLYield 68.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(trifluoromethyl)indan-1-one (2.20 g, 11 mmol) in THF (30 mL) was added sodium borohydride (0.50 g, 13 mmol). After being stirred for 30 min, methanol (10 mL) was added slowly. Stirring was continued for 2 hrs. The reaction was quenched by addition of an aqueous ammonium chloride solution. The two layers were separated and the water layer was extracted by ether. The combined organic layers were washed with water, brine, dried over MgSO4 and concentrated. Column chromatography on silica (10-15% EtOAC in hexane) gave the title compound (1.52 g, 68%) as an oil. MS calculated for C10H9F3O: (M+H)+ 203. found 185.0 (M−H2O+1)+.

Workup

  1. stirringStirring
  2. waitwas continued for 2 hrs
  3. customThe reaction was quenched by addition of an aqueous ammonium chloride solution
  4. customThe two layers were separated
  5. extractionthe water layer was extracted by ether
  6. washThe combined organic layers were washed with water, brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7a8e055019524568a6276eb9bf393049
Source dataset
uspto-grants-2012_09
Patent number
US08268826B2

Reaction notes

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